skeletal equation of carboxylic reactions

Question

Write a skeletal equation for the reaction of ethanoyl chloride with phenyl amine (represented as R-NH2).

What is the chemical term for the bond formed between the two reagents? What term might biologists use to describe this bond

Answer 1

One way to think about this is by identifying which reagent is the nucleophile and which one is the electrophile. Then, you make the available lone pair electrons from the nucleophile add to the electrophilic center (the atom with the highest partial positive charge - check your resonance structures!) of the electrophile.

 

This intermediate species will generally need to collapse to a more stable product, often ejecting a leaving group (good leaving groups are usually weak bases, or better, conjugate bases of strong acids) to give an overall "addition-elimination" reaction.

 

The product will be a functional group (examples of functional groups are ketones, alcohols, amines, etc.) that is biologically relevant (HINT: protein has lots of them).

 

Hope this helps,

 

Jack B.